Chemoselective reduction of organoselenocyanates to diselenides and selenolates

被引：54
作者：
Krief, A
Delmotte, C
Dumont, W
机构：
[1] Department of Chemistry, Fac. Univ. Notre-Dame de la Paix, Namur
来源：
TETRAHEDRON | 1997年 / 53卷 / 36期
关键词：
D O I：
10.1016/S0040-4020(97)00548-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Selenocyanates produce selenolates or diselenides on reaction with metal hydrides (NaH, LiHBEt3, LiBH4, NaBH4). The former transformation is performed with 2 molar equivalents of sodium hydride or lithium triethyl borohydride or 1.25 molar equivalent of metal borohydrides. The second one is performed with lower amount of reducing agent (1 molar equivalent of sodium hydride or lithium triethyl borohydride or 0.25 equivalent of metal borohydrides). Intermediate formation of a selenol or a selenolate which reacts on the unreacted selenocyanate is suspected in the later transformation. (C) 1997 Elsevier Science Ltd.
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收藏
页码：12147 / 12158
页数：12
相关论文
共 62 条
  • [1] Back T. G., 1987, CHEM ORGANIC SELENIU, V2, P91
  • [2] A CAVEAT CONCERNING THE USE OF N-(PHENYLSELENO)PHTHALIMIDE AND TRI-NORMAL-BUTYLPHOSPHINE FOR THE CONVERSION OF ALCOHOLS TO SELENIDES - FORMATION OF 3-PHTHALIMIDO DERIVATIVES FROM AN ALLYLIC 3-STEROL
    BACK, TG
    MCPHEE, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) : 3842 - 3843
  • [3] Concerning o-nitrophenyl-selencyanide and o-amino selenophenol.
    Bauer, H
    [J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1913, 46 : 92 - 98
  • [4] Information on several aryl-selenium-glyconic acid
    Behaghel, O
    Rollmann, M
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1929, 123 (10/12): : 336 - 345
  • [5] Information on aryl-selene halogenide (II Announcement)
    Behaghel, O
    Seibert, H
    [J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1933, 66 : 708 - 717
  • [6] BEHAGHEL O, 1932, CHEM BER, V65, P812
  • [7] BRINTZINGER H, 1948, Z ANORG CHEM, V256, P75
  • [8] HETEROCYCLIC SYNTHESIS USING NEW HETERODIENOPHILES
    BRYCE, MR
    BECHER, J
    FALTHANSEN, B
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1992, 55 : 1 - 29
  • [9] Chierici L., 1954, B SCI FAC CHIM IND B, V12, P56
  • [10] SYNTHESIS OF SELENOACETALS
    CLAREMBEAU, M
    CRAVADOR, A
    DUMONT, W
    HEVESI, L
    KRIEF, A
    LUCCHETTI, J
    VANENDE, D
    [J]. TETRAHEDRON, 1985, 41 (21) : 4793 - 4812
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